Hi, you should come off of anon so that we can discuss this directly! There’s nothing dumb about asking and I’m sure you have a lot of questions. I’d be happy to discuss them with you.
In simplest terms, cuckolding is a situation in which you sleep with other men (or women?) of your choosing while your boyfriend remains faithful to you. This can be whatever you want it to be. A mistake people often make when deciding to explore a fetish is looking up “the way it’s supposed to be done” online. Then they see weird, irrelevant pornography that turns them off to the whole idea.
Perhaps your boyfriend has some ideas about what would turn him on most, but you’ll have to discuss that with him to figure out what they are. Entertain the idea of having multiple friends with benefits on the side while still having a committed and loving relationship with your boyfriend. When you get home from having fun with others, you tell him all about it and drive him crazy with arousal. At that point you decide whether you’d like round 2 or a massage. Cuckolding can be that simple, and that fun. Everything else is up to the two of you and what turns you on.